Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H17NO3 |
| Molecular Weight | 223.2683 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O
InChI
InChIKey=GVEZIHKRYBHEFX-NQQPLRFYSA-N
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21873051 | https://www.ncbi.nlm.nih.gov/pubmed/26005023 | https://www.ncbi.nlm.nih.gov/pubmed/23754252
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21873051 | https://www.ncbi.nlm.nih.gov/pubmed/26005023 | https://www.ncbi.nlm.nih.gov/pubmed/23754252
Cerulenin ((2R,3S)-2,3-epoxy-4-oxo-7,10-trans, trans-dodecadienoylamide) is an antifungal antibiotic isolated from Cephalosporium caerulens, that inhibits eukaryotic lipid and sterol synthesis and blocks lipid modification of proteins. Cerulenin is a potent inhibitor of fatty acid synthase (FAS). It inhibits all known types of FASs: both multifunctional enzyme complexes (Type I) (from yeast, rat liver, mammalian cells, and certain bacteria) and unassociated enzymes (Type II) (from most bacteria, and higher plants). Cerulenin blocks the synthesis of polyketides in a wide variety of organisms, including actinomycetes, fungi, and higher plants. In addition, cerulenin is suggested to inhibit the condensation step in polyketide synthesis as well as fatty acid synthesis. Cerulenin has a wide range of antimicrobial activity, the drug significantly inhibits the growth of yeast-like fungi, such as Candida, Saccharomyces, and Cryptococcus. Cerulenin is commercially available as a biochemical reagent for widespread use in the field of obesity, cancer biology, posttranslational protein modification system, drug discovery research and so on.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Bactericidal activity and mechanism of action of AZD5847, a novel oxazolidinone for treatment of tuberculosis. | 2014 |
|
| Inhibition of fatty acid synthase in melanoma cells activates the intrinsic pathway of apoptosis. | 2011-02 |
|
| Fatty acid synthesis is a therapeutic target in human liposarcoma. | 2010-05 |
|
| Fatty acid synthase as a potential therapeutic target in cancer. | 2010-04 |
|
| Chemical genetic profiling and characterization of small-molecule compounds that affect the biosynthesis of unsaturated fatty acids in Candida albicans. | 2009-07-17 |
|
| Fatty acid synthase inhibition results in a magnetic resonance-detectable drop in phosphocholine. | 2008-08 |
|
| Monosaccharide-induced lipogenesis regulates the human hepatic sex hormone-binding globulin gene. | 2007-12 |
|
| Inhibition of fatty acid synthase induces endoplasmic reticulum stress in tumor cells. | 2007-02-01 |
|
| Inhibition of fatty acid synthase prevents preadipocyte differentiation. | 2005-03-25 |
|
| Inhibition of fatty acid synthase expression by 1alpha,25-dihydroxyvitamin D3 in prostate cancer cells. | 2003-05 |
|
| Cerulenin mimics effects of leptin on metabolic rate, food intake, and body weight independent of the melanocortin system, but unlike leptin, cerulenin fails to block neuroendocrine effects of fasting. | 2001-04 |
|
| Inhibition of beta-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism. | 2001-03-02 |
|
| A new class of antituberculosis agents. | 2000-08-24 |
|
| Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. | 2000-06-02 |
|
| Novel approaches to the treatment of hepatitis C virus infection. | 2000-03 |
|
| Antimycobacterial activity of cerulenin and its effects on lipid biosynthesis. | 1999-02 |
|
| Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis. | 1998-06 |
|
| In vitro activities of free and liposomal drugs against Mycobacterium avium-M. intracellulare complex and M. tuberculosis. | 1993-12 |
|
| Thiolactomycin resistance in Escherichia coli is associated with the multidrug resistance efflux pump encoded by emrAB. | 1993-06 |
|
| Activities of fluoroquinolone, macrolide, and aminoglycoside drugs combined with inhibitors of glycosylation and fatty acid and peptide biosynthesis against Mycobacterium avium. | 1993-04 |
|
| Inhibitors of HIV-1 protease. | 1992 |
|
| Characterization of N-myristoyl transferase inhibitors and their effect on HIV release. | 1991-08 |
|
| In vitro inhibition of HIV-1 proteinase by cerulenin. | 1990-02-26 |
|
| Synthetic non-peptide inhibitors of HIV protease. | 1989-09-15 |
|
| Processing of the structural proteins of human immunodeficiency virus type 1 in the presence of monensin and cerulenin. | 1988-12 |
|
| Inhibitory effect of cerulenin and sodium butyrate on germination of Candida albicans. | 1983-09 |
Sample Use Guides
SCID mice were treated with Cerulenin 15 and 30 mg/kg every 3 days
Route of Administration:
Intraperitoneal
To measure the cytotoxicity of cerulenin against HCT116 and RKO cells, 3x103 cells were plated per well onto 96-well plates. Following overnight culture, cerulenin and oxaliplatin were added at specified concentra¬tions. After 24 h of incubation, cell viability was measured by the mitochondrial activity in reducing 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetra¬zolium monosodium salt (WST-8) to formazan using a Cell Counting kit-8 (Dojindo Laboratories, Kumamoto, Japan). Cells were incubated with a reagent according to the manufac¬turer's instructions. Plates were read at A450 on a spectrometer.
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DB01034
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MF286Y830Q
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Cerulenin
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m3273
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PRIMARY | Merck Index |
SUBSTANCE RECORD
